Synthesis of 3-aminooxindoles via acid-promoted cyclization of α-imino-N-arylamides and α-azido-N-arylamides

Li, Dianjun; Ma, Haichao; Yu, Wei

doi:10.1016/j.tet.2015.12.054

Cited by 7 publications

(3 citation statements)

References 63 publications

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“…BF 3 ·OEt 2 -catalyzed intramolecular Friedel–Crafts reaction was described by Yu et al to synthesize 3-aminooxindole derivatives 397 . Treatment of 2-( N -arylcarbamoyl)-2-iminoacetates 395 with 2 equiv of BF 3 ·OEt 2 in anhydrous CH 3 CN at 80 °C for 1.5 h, afforded 3-aminooxindoles 397 in 72–92% yields.…”

Section: Friedel–crafts Reactionsmentioning

confidence: 99%

α-Imino Esters in Organic Synthesis: Recent Advances

2017

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α-Imino esters are useful precursors for the synthesis of a variety of types of natural and unnatural α-amino acid derivatives, with a wide range of biological activities. Due to the adjacent ester group, α-imino esters are more reactive relative to other types of imines and undergo different kinds of reactions, including organometallics addition, metal catalyzed vinylation and alkynylation, aza-Henry, aza-Morita-Baylis-Hillman, imino-ene, Mannich-type, and cycloaddition reactions, as well as hydrogenation and reduction. This review discusses the mechanism, scope, and applications of the reactions of α-imino esters and related compounds in organic synthesis, covering the literature from the last 12 years.

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Section: Friedel–crafts Reactionsmentioning

confidence: 99%

α-Imino Esters in Organic Synthesis: Recent Advances

2017

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“…Organic compounds having 2-oxindole as a part of their structural units have been found to possess numerous biological activities such as antileishmanial, antitubercular, antimicrobial, antiviral, α-glucosidase inhibitory, tyrosinase inhibitory, antioxidative, antirheumatoid arthritis, intraocular pressure reducing, and PAK4 inhibitory activities. , Consequently several synthetic methods were developed to access 3-functionalized 2-oxindoles . In particular, 2-oxo-3-aminoindoline-3-carboxylates were synthesized from isatin-derived ketimines, acid-promoted cyclization of α-imino- N -arylamides, amination of 3-chloro-2-oxoindoline-3-carboxylate, and cross-dehydrogenative coupling . In continuation of our work toward the development of novel organic transformations, herein we report an unprecedented five-component condensation reaction of isatin, malononitrile, piperidine, alcohols, and molecular oxygen to yield 3-functionalized 2-oxindoles.…”

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confidence: 99%

One-Pot, Five-Component Condensation Reaction of Isatin, Secondary Amines, Malononitrile, Alcohols, and Molecular Oxygen to Access 3-Functionalized 2-Oxindoles

Bora,

Newar,

Maurya

2023

J. Org. Chem.

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An efficient five-component condensation reaction of isatin, malononitrile, secondary amines, alcohols, and molecular oxygen was discovered. The reaction was performed in a one-pot fashion, and it does not require any metal catalyst. It gives straightforward access to structurally diverse 2-oxo-3-aminoindoline-3-carboxylates in moderate yields (70−88%). The scope of the reaction was successfully demonstrated by synthesizing a series of 3-functionalized 2-oxindoles by varying the isatin, amine, and alcohol components.

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“…Performing the reaction on 1.1 mmol scale (0.262 g) of ketimine 1a , selenones 2a (0.34 g), and benzaldehyde (0.233 g) produced the desired product 3a in 51% yield (0.2 g). To gain mechanistic insight, we subjected the preformed amine 4 and selenone 2a to our reaction condition in the absence of NHC-catalyst and benzaldehyde. The desired product was obtained in a 35% yield (Scheme ).…”

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confidence: 99%